We had a lovely Labor Day weekend in Annapolis. The weather was marvelous, the temperatures finally cooled, and watching this summer come to an end was cause for celebration. It was the summer that never really happened. We bid it farewell.

In the coming days, the weather will continue to cool down as the days grow shorter. With kids back at school (in whatever form that takes), we start thinking about fall boating, one of my favorite times of year.

In the Pacific Northwest, Labor Day means the Bumbershoot Music Festival in Seattle, and then there is the Port Townsend Wooden Boat Festival. I always enjoyed September on boats in the San Juan Islands. Places like Roche Harbor are busy this time of year. It is also time to make my first batch of hot buttered rum batter to keep in the freezer.

Autumn in New England brings its explosion of fall color, which will soon start in northern Maine and move south in the coming weeks, providing us with fabulous scenery from New England down through Connecticut, New York, and New Jersey.

The Chesapeake Bay calms down in the fall, as causal boaters are off the water, for the most part, and sailing and cruising are at their best, with cool weather, good breeze, and humidity so low one can see Thomas Point Shoals Light from Annapolis. A weekend on the water is all about great sailing, ports and hatches open, serene anchorages and cool evenings in the cockpit and flybridge. I look forward to getting out my favorite fleece jacket, a cozy alternative to summer’s heat. Even the bugs go away.

fall boating in annapolis maryland

(Seen above: The sun sets on a marina at Beards Creek in Annapolis, Maryland. Photo Cred: wreditor on reddit.com)

There will be no fall boat shows in Annapolis this year, a sad but inevitable result of the continued caution with Covid-19.

I will miss seeing the familiar faces of exhibitors I have known for 25 years, although most of us have retired. Many still come back for the same reasons I do. We walk the docks with the crowds, look at what new technology brings us in boats and equipment. I will miss the obligatory roast beef sandwich at the Fleet Reserve Club, a charity event that has been a fixture of the shows for years. Power or sail, I enjoy both shows.

This is also the time when cruisers from Canada, and those who spent the summer in New England, are on the move south, a migration that is as much a part of this season as pumpkins and falling leaves. I live on Ridout Creek off Whitehall Bay, and it is great fun to see boats from all over the world come anchor for a day or two in my backyard, taking a break from long days moving south.

Many plan their travels through Chesapeake Bay to coincide with the Annapolis boat shows. Some come to replace the boat hook that is always on sale at West Marine or buy new boat shoes at Fawcetts. If you want to upgrade your electronics, get a new anchor, self-steering gear, windlass, or arrange a charter, this is the place, especially at the sailboat show, which is the largest show of its kind. Company reps are on hand to answer questions, sell systems, so subject matter expertise is easy to find. Just about anything even remotely related to boating is here. And there are always deals and boat show specials.

Some south-bound cruisers work the shows. They help move boats into place on the floating docks, put on wristbands as people hand over their tickets, and assist show management in all sorts of activities. The town really buzzes during these shows, as the Naval Academy moves into its football season. Crowds are everywhere, and the energy is wonderful.

At the conclusion of each show, especially the powerboat show, delivery crews hustle their yachts away from the floating docks and make a beeline for Ft. Lauderdale. With little time to spare, they must get to Florida as soon as possible to make the huge international show. Having been on several of these deliveries, these are long days and the weather be damned.

annapolis power boat show 

(Seen above: The Annapolis Power Boat Show in 2019, but unfortunately the 2020 show has been cancelled. The Ft. Lauderdale Boat Show is still moving forward!)

One year I asked to crew on a large, full displacement trawler that had been recently unloaded off a ship from Taiwan. Our crew consisted of a local licensed yacht captain, his friend, who is a merchant marine academy grad who drives an offshore tug for a living (and who had just towed an aircraft carrier from Hawaii to California and was on holiday), a fellow whose new boat was under construction and he wanted the experience, and the fire chief of a local fire department.

As it was a new boat with no equipment, not a roll of paper towels, knives and forks, or even toilet paper. So, we loaded aboard a liferaft, safety gear, plotter, radio, radar, and bags of stuff. We provisioned with only the essentials. In literally a few minutes, we took off right after the show ended, as workers broke apart the sections of floating docks holding us captive, motoring off as the sun set, while we jury-rigged the electronics to get them working before total darkness came.

Out in the Atlantic Ocean, passing Cape Hatteras, the Coast Guard called us and instructed us to stay offshore and to not even think about coming in, as the inlet was closed from the stormy seas now building from an approaching nor’easter. We somehow stayed just ahead of the worst of the storm, but the untested new trawler gave us a punch list of things that needed attention from the rocking and rolling. Anchor chain slapping against the hull every few seconds made it difficult to sleep in the forward stateroom. And the engine-heated hot water made the shower plumbing fixtures close to 200 degrees, dangerously hot, and it was hard to avoid making contact in the rolling seas.

When it was time to go inside to the ICW in Florida, the skilled delivery captain pushed the throttle to WOT as the 58-foot trawler surfed down large waves into the narrow inlet, corkscrewing our way in, way above hull speed. I had white knuckles from that dramatic entrance, but we made it to Bahia Mar in Ft. Lauderdale just in time. The boat cleaning crew was there on the dock, ready to step aboard and get her ready for the upcoming boat show. We hurriedly gathered our stuff and got off the boat, which was now covered in the salt and sea slime from days offshore in rough weather. And people call this fun!?!

nordic tug boat cruising

(Seen above: Nordic Tugs make excellent long-range cruising boats whether heading south or to the islands.)

Which brings up a good question.

Will we head south this year for the winter? My current boat is a Hunt Harrier 25, a simple day cruiser. It is no cruising boat, so she stays on her lift at home. But I do get the cruising itch about this time of year. Thoughts of spending a winter in Stuart, St. Augustine, Fort Meyers, or Marathon come strong with the first hint of autumn.

It will not be long before we wake up to sea smoke on the creek, and temperatures will soon get nippy. Recent winters have been mild around here, but the luscious smell of tropical plants and flowers, Cuban sandwiches from Publix, crystal clear water, and the camaraderie of the wintertime liveaboard community are strong attractions.

I have traveled between Annapolis and Florida on the ICW numerous times, and each has been different…and wonderful. Every journey up or down the ICW is an adventure. I have done it in company with other boats, I have done it with crew, as crew, and solo. So, I speak from experience.

Let me get a read from some friends and put together thoughts and comments about doing this ICW trip south in 2020, during these cautious times. And how best to make it just as memorable, and safe.